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Jon Lester would’ve said ‘probably yes’ to 5-year/$120 million offer last spring from Red Sox 12.18.14 at 8:46 pm ET
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Former Red Sox pitcher and current Cubs pitcher Jon Lester joined the Hot Stove show Thursday night with Mike Mutnansky, Rob Bradford and Alex Speier to discuss what the free agent process was like, what the negotiations last spring training were like with the Red Sox, and also what it was like the hours and days following officially signing with the Cubs.

Lester signed with the Cubs for six years and $155 million, with a vesting option for a seventh year.

Everyone keeps coming back to the reported 4-year/$70 million offer the Red Sox gave to Lester during spring training last season. What if the Red Sox came in with a higher offer — such as the Cliff Lee, 5-year/$120 million deal — would Lester have accepted?

“That is one of those deals where hindsight is 20/20. You go back in time and you look at it and you go, ‘probably yes,'” said Lester. “I mean you don’t know. I mean it is one of those deals where when it is sitting in front of you that is a lot of money to turn down. That would have made it very difficult to turn it down.”

Following spring training, Lester and his camp were under the impression the two sides would not discuss a contract during the season because that was what was agreed between them and the Red Sox, and they didn’t want any distractions for he and his teammates during the year.

“As far as I understood, and that is not coming from my agent, that is from what I understood coming out of everyone’s mouth was that once the season started, I think we had all agreed upon that and it wasn’t just one side saying we don’t negotiate during the season,” Lester said. “I think it was more a group discussion and a group decision that if we weren’t able to come to a conclusion with the contract negotiations before the season started we thought it was in the best interest of everybody to table it ’till the offseason and wait until the season is over and all the distractions of playing, the ups and downs of the season and all that to get after it again.

“Like I said the other day, I don’t know if that is a bad quality or a good quality, but I am kind of hard-headed when it comes to that. If we make a decision one way or the other, just like if we would have made the decision to continue talking I would have expected that to continue. I think we all kind of decided at that time with the distractions of everything going on it wasn’t the right time or place to continue the discussions.”

Following are more highlights from the interview. For more Red Sox news, visit weei.com/redsox.

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Read More: Dustin Pedroia, Jon Lester, Theo Epstein,
Jon Lester: Trade to A’s ‘broke that barrier’ about leaving Red Sox as free agent 12.15.14 at 2:50 pm ET
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Jon Lester, at the press conference introducing him with the Cubs upon the completion of his six-year, $155 million deal, said that the Red Sox‘ decision to trade him to the A’s at the July 31 deadline (along with Jonny Gomes in exchange for outfielder Yoenis Cespedes) did impact his view of the free agent process. Lester said that it became easier to imagine changing organizations once he experienced success with a new club. (After going 10-7 with a 2.52 ERA in 21 starts with the Red Sox, Lester went 6-4 with a 2.35 ERA in 11 starts for the A’s.)

“I think so,” Lester told reporters of whether being traded impacted his approach to free agency. “We were traded. That was the unknown of going to a whole different coast, a whole different organization, a whole different philosophy. I think going there prepared us for this time. I think if we finished out the year in Boston and you get down to this decision, I think it would be a lot harder. Not to say it wasn’t hard as it was, but that broke that barrier of, ‘I wonder if I can play for another team.’ I think we answered those questions.”

Still, Lester acknowledged that he agonized over the decision-making process, particularly the final determination about whether to return to Chicago, return to Boston (which offered a six-year, $135 million deal) or consider the interest of West Coast suitors (most prominently the Giants). He fielded countless calls from teammate Dustin Pedroia (among others) before coming to terms with his decision.

“I kind of describe the process in two different forms. I think when you’re sitting there meeting with people, we got to come to Chicago, meet with these guys, enjoy dinner. We had some other teams that came into our house, meet with those people. I think that’s kind of the fun, exciting time. You get to hear different philosophies. You get to meet different people that you probably won’t get to be around. And then you have kind of the second phase where you have to sit down and make a decision. That part, for us, was not fun,” Lester said at the press conference. “That was a lot of phone calls, a lot of minutes sitting down and thinking about what we were going to do. But as far as the decision-making, we made it literally hours before it was probably announced. Just sitting down with these guys, sitting down with my wife, trying to iron it out, it came down to that final moment where we just put our fist down, said, ‘This is it. This is where we’re going to go. This is where we feel the most comfortable.’ We’re not people that are going to put one foot in the pool. We’re going to dive in. That’s what we did.

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Larry Lucchino on M&J on Jon Lester: ‘To a man, we were surprised we didn’t get into a sequential negotiation’ 12.13.14 at 1:34 pm ET
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Red Sox president and CEO Larry Lucchino joined Mustard & Johnson Saturday at Fenway Park during Christmas at Fenway to discuss the Jon Lester contract negotiations and what went wrong, as well as other Red Sox matters. To hear the interview, visit the Mustard & Johnson audio on demand page.

Much has been made of the reported 4-year/$70 million contract the Red Sox offered Lester during spring training last season. Lucchino went into the reasoning behind that offer, and to the Red Sox it was only viewed as a starting point, as the organization wanted to have conversations following that offer.

“We did make a number of efforts to reignite negotiations and I think as Ben has said, we went in just to get the process rolling and we came up with a number — Josh Beckett had signed for $68 million for four years and that was the largest number for a pitcher we had ever given to a non-free agent,” Lucchino said. “We thought that was a principle place to start and that was all that it was perceived to be. For whatever combination of reasons there was a reluctance on the part of…”

“I think we all were surprised,” Lucchino added of the reluctance of the Lester camp to continue negotiating. “Matters of this type are shared along John [Henry], Tom [Werner] and Ben [Cherington] and myself and other folks in the baseball operations department. To a man, we were surprised we didn’t get into a sequential negotiation.”

Lucchino was also asked if he regrets what took place last spring, and he admitted he does because of the final result.

“I think the short answer has to be yes because we didn’t get the job done,” he said. “Our job was to get Jon Lester signed and to make him a long-term member of the Red Sox organization. This is a results oriented business. Finishing second is not our business plan. I wish it had developed differently. I don’t think it does us much good now to replay each step along the way. We felt when we started that we were beginning a negotiation would take place fairly intensively through spring training and perhaps into the season, but certainly through spring training, and that didn’t happen.”

Lester reportedly signed with the Cubs for six years and $155 million with a vesting option for a seventh year. The Red Sox have openly been reluctant to give out long-term deals of late, and that was something the organization was faced with during the Lester negotiations.

“We have to have one eye on the present and one eye on the future,” Lucchino said. “I would tend to think most baseball fans understandably focus on the next year, the next season. One of Ben Cherington’s jobs is, in fact it is a job for all of us in the senior leadership of the Red Sox, is to keep one eye on what is around the corner — the next couple of years, not right now. John Henry is a brilliant analyst. He’s also an imperialist. He looks and he sees what’s happened and puts it together and sees a track record that is less than encouraging with long-term deals in general.  He’s not the only one that has that view.”

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Read More: Jon Lester, Larry Lucchino,
Buster Olney on MFB: ‘With a couple more moves, the Red Sox could easily win this division again’ 12.11.14 at 2:10 pm ET
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Buster Olney

Buster Olney

ESPN’€™s Buster Olney joined Middays with MFB on Thursday to discuss the Red Sox‘€˜ recent moves and to look ahead to the 2015 season. To hear the interview, go to the MFB audio on demand page.

The Red Sox have been very active in the last day or so with adding to their starting rotation. Wednesday night they reportedly traded for Arizona’s Wade Miley and Thursday they traded for Rick Porcello with the Tigers, and also reportedly signed free agent Justin Masterson. Olney feels the way things are going, they are in good shape relative to the rest of the American League East.

“I would say this, Miley, Porcello, you’re talking about No. 3 type starters, but here’s the thing, you have to remember where the Red Sox are in context of this division,” said Olney. “The Orioles are way down, they’ve taken a couple of huge hits during this offseason. The Yankees are in a very murky situation. A lot of older players. The Blue Jays have some real holes on that team. Tampa Bay seems to be taking a step back. I still think with a couple more moves, the Red Sox could easily win this division again, especially with the additions they have made with their lineup.”

Although the team has added three pitchers, none of which are so called “aces.” Olney notes adding a potential No. 1 starter, such as Cole Hamels, may be easier said than done given the current market.

“It’s really not clear whether they are going to get that No. 1 because like a game of musical chairs, the options are certainly drying up,” Olney said. “We’ve been wondering why there hasn’t been talk with the Phillies that we know of about Cole Hamels, as much as we maybe anticipated. They may already know this is something that is not going to happen. They are on his no-trade list for a reason and a lot of pitchers, especially where they are in the second half of their careers, they don’t want to pitch in the American League. They don’t want to go to the American League East. Imagine if you are Cole Hamels and you could try and steer yourself into a situation where you could go back to Southern California where he is from, or you could leave yourself in a position where you have to be the guy to replace Jon Lester in Boston — in terms of comfort level that’s not really close.”

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Tom Verducci on D&C: Wade Miley, Rick Porcello ‘can pitch at All-Star levels’ at 1:01 pm ET
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Tom Verducci (right) says the Red Sox got two "All-Star" quality pitches in Wade Miley and Rick Porcello. (Andrew H. Walker/Getty Images)

Tom Verducci (right) says the Red Sox got two “All-Star” quality pitchers in Wade Miley and Rick Porcello. (Andrew H. Walker/Getty Images)

Sports Illustrated baseball writer and FOX color commentator Tom Verducci joined Dennis & Callahan on Thursday to recap baseball’s Winter Meetings and also was able to give his thoughts on the Red Sox adding pitchers Rick Porcello and Wade Miley. To hear the interview, go to the Dennis & Callahan audio on demand page.

Verducci was on the show right as the Porcello trade broke, so he was able to give instant analysis of both the deals, which he was in favor of given the durability of both Porcello and Miley.

Miley was acquired for Rubby De La Rosa and Allen Webster, while Porcello was acquired for Yoenis Cespedes, Alex Wilson and minor league pitcher Gabe Speier.

“I think, you guys know all the names in their farm system the great arms they do have sitting there, you really do need protection for them so they don’t have to throw so many innings and you have two guys now I think are both really good athletes, really don’t have red flags in their deliveries or stuff, profile well to remain durable,” Verducci said. “That is a very valuable thing. To me that’s always been an underrated skill in the game — is durability. Can you do it year-after-year? And these guys can. They have protection and they are pretty good pitchers too. It’s not like they just got guys who are so called innings eaters — the Edwin Jackson‘s of the world — they got two really good pitchers who can pitch at All-Star levels.”

Added Verducci on Porcello: “Makes sense to me. Teams like flexibility, the fact that both of these guys are in the last year before free agency, not a bad thing for either team. I really like Ricky Porcello. He’s a lot younger than you think. I think he is 26, 27 years old. The way he has incorporated his curve ball the last few years I think has brought him to another level.

“A ground ball pitcher, make sure you have a good defensive infield behind you because he suffered for that in Detroit for most of those years when they didn’t have a lot of range behind him. Total gamer. You guys remember the fight at Fenway a few years ago. Pitched in a big game when he was 20 years old, Game 163. That is exactly the kind of move I would do if I was the Red Sox — flip Cespedes for a year of Ricky Porcello.”

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Read More: Jon Lester, rick porcello, Tom Verducci, wade miley
The Red Sox and the quest for innings and left-handedness in their starting rotation 12.10.14 at 8:59 pm ET
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SAN DIEGO — In five full big league seasons from 2010-14, Clay Buchholz has averaged 145 innings. In his first season as a full-time big league starter in 2014, Joe Kelly logged 96 1/3 innings. Those are the only two known members of the 2015 Red Sox.

Neither pitcher has a demonstrated, reliable ability to handle a full-season workload of 200 innings. As such, the Red Sox may prioritize pitchers whose track records suggest the potential to do just that.

We always go through an exercise in budgeting, or coming up with a budget number of innings that need to be accounted for,” said Sox manager John Farrell. “You take into account what individual pitchers have done in previous years and what you project them to be able to provide upcoming. We knew going in that there were going to be a couple of spots needed for innings eating and very quality innings pitched. Ideally, if you can get a couple of 200-inning pitchers, they don’€™t go on trees, but that’€™s the goal.”

That might help to explain some of the Sox’ interest in Diamondbacks lefty Wade Miley, who has logged at least 198 innings in each of the last three seasons. The need for innings stability might also have the Sox particularly intrigued by pitchers like Jordan Zimmermann (203 innings a year for the last three years) and Rick Porcello (who threw 200 innings for the first time in 2014 but has never been on the DL). Other potential targets such as free agents James Shields (averaging an astounding 233 innings a year over the last four years) and Ervin Santana (averaging 207 innings a year for the last five seasons) might gain prominence as Sox targets for the same reason.

Ideally, the Red Sox would like to add a left-hander to their rotation as well given that, for now, their only two starters (and, in all likelihood, all the candidates for the fifth starter’s spot) are right-handed. However, Farrell suggested that the necessity of having a lefty in the rotation has diminished in recent years in the American League East.

I think you always like to have that at your disposal to match up or to map out your rotation how it might fall depending on the upcoming schedule,” said Farrell. “[But] when you look at what’€™s changing in our division, this once was and just was a few years ago a very left-handed hitting division. That’€™s shifting, when you see the changes that have gone in Toronto, in Baltimore, probably with some changes that still might take place down in Tampa, that might be the case as well, you’€™re seeing a little bit more right-handed offense starting to emerge in other cities.”

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Read More: 2014 winter meetings, John Farrell, Jon Lester,
Ben Cherington breaks down the breakdown in Jon Lester negotiations at 3:54 pm ET
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SAN DIEGO — As the Cubs celebrate the arrival of their ace in Jon Lester, the Red Sox are left to answer for how it came to this — how a pitcher who expressed a desire to spend his career in Boston, even if it meant a hometown discount, ended up heading elsewhere. Looming over that postmortem is the question surrounding the team’s initial four-year, $70 million offer to Lester last spring — an offer that was so far from what the pitcher deemed acceptable that it became, in essence, the end-point of negotiations until Lester arrived at free agency.

Red Sox GM Ben Cherington — who learned late on Tuesday night of Lester’s decision in two conversations, first with agent Seth Levinson and then in a brief phone call with Lester — addressed some of those issues on Wednesday. While he declined to go into the specifics of the team’s offers (either the four-year, $70 million extension proposal in spring training that was meant to be a conversation-starter rather than an endpoint, or the team’s final six-year, $135 million offer this week (the team’s second offer of the free-agent process, according to Cherington, made this week after an initial offer in November following a meeting between Lester and team officials in Atlanta), which came up $20 million short of what the Cubs had on the table), Cherington offered his view of what happened in the talks with Lester.

I think we would have liked to have had more chance for dialogue prior to the season. Why that didn’€™t happen, maybe there’€™s more than one reason. I think we can certainly learn from the process. But we desired to have more dialogue prior to the season and made an effort during the season and weren’€™t able to,” said Cherington. “Then we got into free agency and we’€™re able to do it then. Jon did a lot of great things for the Red Sox. We wish him nothing but the best. We’€™re moving on.”

Here are some highlights of Cherington’s 30-minute media session:

ON THE FOUR-YEAR, $70 MILLION OFFER AND TALKS BETWEEN LESTER AND THE RED SOX ABOUT AN EXTENSION

“The problem when pieces of conversations or pieces of information get put out without the whole context of what’€™s going on, it can sort of shape the public narrative. All I can say is that we had a lot of conversations prior to making an offer. I think there was a decent understanding on both sides of where, back in spring training, and during the season, of where the sort of range of both sides were looking. We felt that we could enter into a conversation, and we could start a conversation and that’€™s the only way you get to a deal, is to start a conversation. We just weren’€™t able to have the kind of dialogue back in the spring, or during the season, that we wanted to. as I’€™ve said before, can we learn things from what happened? Sure. Always can. But right now, once you get into free agency, it becomes a different animal. We understand that. Simply put, the Cubs offered more than we did and he made a choice and we respect it and wish him nothing but the best. We go back to focusing on putting our team together and we feel really good about where we are.”

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Read More: 2014 winter meetings, ben cherington, Jon Lester,
Jon Lester to Red Sox Nation: ‘I understand the disappointment’ at 1:31 pm ET
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Hours after accepting a six-year deal to join the Cubs, Jon Lester sent a tweet to fans of the Red Sox in an attempt to soothe some hard feelings.

Wrote Lester: To Red Sox Nation, I understand the disappointment. Boston will always have a big place in my heart and we’ll always consider y’all family!

Continued Lester: Extremely difficult decision for me and my family but we love the outcome and couldn’t be more excited to join the Cubs organization!

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Poll: Should Red Sox have upped offer to sign Jon Lester? at 9:12 am ET
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Jon Lester decided to accept a reported six-year, $155 million deal with the Cubs late Tuesday night. The Red Sox apparently did not offer near that much money.

How do you feel about the Red Sox refusing to match the Cubs’ offer?

Should the Red Sox have upped their offer to sign Jon Lester?

  • No, a six-year, $155 million deal for a 31-year-old pitcher is not smart business (69%)
  • Yes, they have the money and they should have spent it (31%)
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Source: Cubs, Jon Lester agree to 6-year, $155 million deal at 1:36 am ET
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Jon Lester's Red Sox career is now in the rearview mirror. (Jim Rogash/Getty Images)

Jon Lester‘s Red Sox career now is in the rearview mirror. (Jim Rogash/Getty Images)

SAN DIEGO — Almost a year after his proclaimed interest in returning to the Red Sox on a hometown discount, left-hander Jon Lester rejected his former team’s free agent overtures and instead chose to make his baseball home in Chicago with the Cubs, according to an industry source.

Lester agreed to a six-year, $155 million deal, the largest average annual value ($25.83 million) ever given to a pitcher on a multi-year deal in free agency. His deal with the Cubs includes a vesting option for a seventh year. The Sox’ final offer, according to another industry source, was for a six-year, $135 million deal with no seventh-year vesting option.

Lester’s decision followed a weeks-long process of visits with interested teams and two full days at the Major League Baseball winter meetings in which much of the industry’s activity seemed to depend upon his decision.

“You just wait for the white smoke,” Cubs manager Joe Maddon joked on Tuesday afternoon of the wait for Lester’s choice between his team, the Red Sox, Giants and Dodgers. “This is a guy when the game is really big he was always at his best. To possibly get this opportunity to work with him for the first time is very exciting. … [You] can’t have any more respect for a baseball player than we do for him now. For us to be able to pull this off it would be pretty outstanding.”

In choosing to sign with the Cubs, Lester joins a front office with whom he has a great deal of familiarity. Cubs president of baseball operations Theo Epstein, general manager Jed Hoyer and assistant GM Jason McLeod all have close relationships with the pitcher after spending years with him in the Red Sox system.

A case can be made that the fact Lester chose that group rather than a Sox organization with whom he spent the first 12 years of his career represented a particularly painful dagger for Boston. Lester was the first player drafted under the current Sox owners in 2002 and contributed to two World Series titles, foremost with a dominant performance for the ages in the 2013 postseason.

Lester had made no secret of his desire to return to the Red Sox, stating in no uncertain terms prior to the 2014 season that he would take less than full market value in hopes of remaining with the Sox for his entire career. But when the Sox made an initial four-year, $70 million offer to Lester in spring training, the pitcher and club saw insufficient common ground to continue talks during the season, and Lester didn’t re-open the door to in-season negotiations.

Still, even after the team traded Lester (and Jonny Gomes) to the A’s at the trade deadline for Yoenis Cespedes, the Sox remained adamant that they’d make a run at the pitcher when he arrived at free agency after the season following a 16-11 season in which he had a career-best 2.46 ERA and 220 strikeouts in 219 2/3 innings. That is precisely what they did, with team ownership meeting with him in the Atlanta area in November and principal owner John Henry traveling back to meet with the pitcher one-on-one again last week. The team showed a willingness to go to six years — the longest guarantee ever made under the Henry ownership group.

But ultimately, Lester, 30, opted to be a part of Chicago’s effort to end its 106-year championship drought. The Red Sox, who have two holes in their rotation, must now focus their attentions elsewhere as they pursue a top-of-the-rotation option for 2015 and beyond.

Read More: 2014 winter meetings, cubs, Jon Lester,
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